4-Phenoxyphenylboronic acid → HCID 71113493, compound

HRID 1522281Notes

Reaction equation

HRID 1522281 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[O:10]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH:26][CH:27]1[CH2:40][C:29]2([CH2:32][N:31]([C:33]([O:35]C(C)(C)C)=O)[CH2:30]2)[CH2:28]1.[F:41][C:42]1([F:52])[CH2:45][N:44]([CH2:46]/[CH:47]=[CH:48]/C(O)=O)[CH2:43]1>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([O:26][CH:27]2[CH2:28][C:29]3([CH2:30][N:31]([C:33](=[O:35])/[CH:48]=[CH:47]/[CH2:46][N:44]4[CH2:45][C:42]([F:52])([F:41])[CH2:43]4)[CH2:32]3)[CH2:40]2)[C:2]=1[C:14]1[CH:15]=[CH:16][C:11]([O:10][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 52987765tert-Butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylateHCID 86721855HCID 86721855, compound

Product 1

HCID 71113493HCID 71113493, compoundYield 2.7%

Procedure

(E)-1-(6-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)-2-azaspiro[3.3]heptan-2-yl)-4-(3,3-difluoroazetidin-1-yl)but-2-en-1-one was prepared 5,6-dichloropyrimidin-4-amine, 4-phenoxyphenylboronic acid, tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate and (E)-4-(3,3-difluoroazetidin-1-yl)but-2-enoic acid with method S1, S2, S3, S4A. Yield 2.7%. 1H NMR (CD3OD) δ 8.31 (s, 1H), 7.10-7.47 (m, 9H), 6.60 (m, 1H), 6.40 (t, 1H), 5.25 (m, 1H), 4.54 (qt, 4H), 4.27 (d, 2H), 4.08 (s, 1H), 4.00 (m, 3H), 2.74 (m, 2H), 2.27 (m, 2H). HPLC PURITY: 95%, MS: m/z=534[M+H]+

Sources & evidence

ORD record
ord-6cf3aaf54cca4a559004d2ab7175f434
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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